Enantioselective Construction of Axially Chiral Azepine-Containing P,N-Ligands from L-Alanine

A family of axially chiral azepine-containing seven-membered cyclic P,N-ligands (named Indole-azepinap) have been prepared by using L-alanine as an original chirality source. The direct chromatographic separation of two diastereomeric phosphine oxides on silica gel enabled these ligands to be easy available, allowing further structural and electronic modifications. Preliminary application of these Indole-azepinaps has been demonstrated in a Pd-catalyzed asymmetric allylic alkylation with high yields and moderate enantioselectivities.

Automated summary

A family of axially chiral azepine-containing seven-membered cyclic P,N-ligands, named Indole-azepinap, was prepared using L-alanine as an original chirality source. The direct chromatographic separation of two diastereomeric phosphine oxides on silica gel allowed easy accessibility of these ligands for further structural and electronic modifications. These Indole-azepinaps showed promising results in a Pd-catalyzed asymmetric allylic alkylation with high yields and moderate enantioselectivities.